Short version:

I looked like a dork today. Is it the skirt, the shoes, the combination or something else? Help. Here's some shoes I tried on today. I would NOT be wearing dark hose with the lighter shoes, of course. Can't wear jeans to work. Can't tolerate high heels. Only work (volunteer) one day a week. Don't want to spend a lot of money on special volunteering clothes/shoes. Thanks!

Long version:

Ahh. The DFS saga continues. This is my business casual outfit I wore today (aka 101 ways to wear your only black dress skirt). Somehow the top half didn't look as cheeky as I'd hoped. Angie says I need to get the Gap really skinny pants and my troubles will be over. Maybe she's right. I like skirts, but somehow with flats they look frumpy fast.

I stopped at Last Chance on my way to look for some more modern shoes. Here's a smattering of what I tried on. (I bought nothing.) While I was trying on, a woman asked me for advice on some shoes (You can see her seated behind me in pic. 5. I have on low heeled black oxfords, she's wearing a beret.) We chatted a bit. She said I had beautiful skin and asked me how old I was. I told her, "46". She seemed surprised, like I looked *older* than 46. She said, "Wow, you could take 10 years off your look if you just put a little more color in your hair and change the way you dress!" Pointing to the oxfords, she said, "Those are grandma shoes." (BTW she was 49 years old.)

I said, "Yes they're very trendy now, but maybe they'd look better on a younger person." She kept gushing about how young I'd look if I just "put a liitle more (?) color in my hair," and how "the way I was dressing was aging me." I just smiled and kept going about my business. Except for feeling my mouth drying up unexpectedly, I remained surprisingly calm.

Now, before all of you wonderful friends rush to my defense, the main reason I'm telling you this story is so you can help me pinpoint where the frump is. I want to look at myself objectively. I know this woman was just a stranger (and I remembered Angie's jodphur jeans story) so I'm prepared to let her comments roll off my back, BUT if *she* thought I looked frumpy, chances are other people might too. While I was driving I asked myself if it was important to me to be perceived by *most* people on the street as stylish and well dressed; the answer is yes.

When I got to the DFS boutique the director was there and she greeted me. I haven't had much time to get to know her, and I can tell she and staff are trying to figure me out. My work outfits are in the "trying and can't" category, so I'm almost stylish but somehow falling short. They kept eyeing my studded boots and football socks last week, lol! Keep in mind I can stand in a flattering pose for my WIW photos, but these gals see the outfit in motion. And sometimes it ain't pretty!

So today my *boss* looked at my shirt and man-tie combo and said, "That's really cute. Not too many people could pull that off!" Ummmmm......? Forgive me if I am a little suspicious of that compliment. I'm not sure if I should read between the lines with that one! By this time I felt like I was dressed like Natalie on "The Facts of Life".

To make matters worse, when I got home today my daughter took one look at me and said, "I really like you in jeans, Mom." She's fifteen. I told her that jeans didn't meet dress code at the boutique and she thought that was a real bummer. Me too!

So about the shoes I tried on:the flats (3 & 9) are the most comfortable and feel the most like *me* but I'm open to branching out. I could wear 3 and 4 to work with nude hose this summer. The open sandals would be for my casual life (6 were the most comfy; hideous with the black hose, huh?). I thought the black oxfords might work with my black skirt (couldn't find a low heeled bootie). Most of these were in the 20-30 dollar range, which isn't bad.

Thanks for sticking with me! Thanks for your analysis in advance.